EP0950674A1 - Procédé de préparation de polyuréthanes thermoplastiques - Google Patents

Procédé de préparation de polyuréthanes thermoplastiques Download PDF

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Publication number
EP0950674A1
EP0950674A1 EP99107087A EP99107087A EP0950674A1 EP 0950674 A1 EP0950674 A1 EP 0950674A1 EP 99107087 A EP99107087 A EP 99107087A EP 99107087 A EP99107087 A EP 99107087A EP 0950674 A1 EP0950674 A1 EP 0950674A1
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EP
European Patent Office
Prior art keywords
und
propanediol
bis
polyaddition products
polyisocyanate polyaddition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99107087A
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German (de)
English (en)
Inventor
Thomas Dr. Servay
Marcus Dr. Leberfinger
Dieter Nitschke
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BASF SE
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BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0950674A1 publication Critical patent/EP0950674A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203

Definitions

  • the invention relates to processes for the production of Polyisocyanate polyaddition products by reacting (a) Isocyanates with (b) isocyanate-reactive compounds with a molecular weight of 451 to 8000 in the presence of (c) Chain extenders and optionally (d) crosslinking agents, (e) catalysts and / or (f) customary auxiliaries and / or Additives as well as those that can be produced with this method Polyisocyanate polyaddition products.
  • thermoplastic polyisocyanate polyaddition products by reacting (a) isocyanates with (b) compounds reactive towards isocyanates with a molecular weight of 451 to 8000 and an average Functionality from 1.8 to 2.6 in the presence of (c) chain extenders, (e) catalysts and / or (f) customary Auxiliaries and / or additives and those obtainable in this way thermoplastic products.
  • thermoplastic Polyisocyanate polyadducts in general also known as thermoplastic polyurethane (TPU).
  • TPU thermoplastic Polyurethane
  • These TPUs are semi-crystalline materials and belong to the Class of thermoplastic elastomers. They consist of one Semi-crystalline hard block, which is made up of the isocyanate and low molecular chain extender builds, and an amorphous Soft block, which is typically contrasted from the higher molecular weight Isocyanate-reactive compounds, usually polyester and / or Polyether diols is built up. The best possible micromorphological Separation of these phases is the necessary prerequisite for the elastic behavior of the TPUs.
  • the hard block acts as a physical network due to its partial crystallinity, which are reversible above the hard block melting point dissolves, which enables the thermoplastic deformation of the material.
  • the soft block is in one at room temperature plastic or liquid state, ultimately it can be reduce the easy deformability of the TPU.
  • the physical Networking enables the elastic return in the initial state.
  • the TPUs are characterized by a combination of advantageous ones Material properties, such as low abrasion, good chemical resistance and high flexibility with a high strength at the same time.
  • Materials properties such as low abrasion, good chemical resistance and high flexibility with a high strength at the same time.
  • they offer advantages through inexpensive production, for example with the belt or the extruder process, the can be carried out continuously or discontinuously, and the simple processing of thermoplastic.
  • products can be used a wide range of properties in a wide range of hardness produce.
  • the heat resistance and thus also the Use properties of the material especially at temperatures above 80 ° C are mainly due to the melting behavior of the hard segment block, i.e. the quality of the physical Networking, determined.
  • thermoplastic polyisocyanate polyadducts in particular thermoplastic polyisocyanate polyadducts
  • TPU thermoplastic polyurethanes
  • TPUs used.
  • Methods of making TPUs are common known and differ from manufacturing processes of non-thermoplastically processable polyisocyanate polyaddition products mainly by chemical Networks in the product largely avoided and thus as compounds (b) which are reactive toward isocyanates, which have an average functionality of 1.8 to 2.6, preferably 1.9 have up to 2.2, particularly preferably 2, and preferably on crosslinking agents, i.e. compounds reactive towards isocyanates with a molecular weight ⁇ 450 and a functionality of ⁇ 3 largely, particularly preferably completely omitted.
  • 1,3- and / or 1,2-propanediol preferably 1,3-propanediol.
  • At least one aromatic Chain extender i.e. at least one connection with one Molecular weight of ⁇ 450 g / mol, two compared to isocyanates reactive groups and with at least one aromatic system in the molecule.
  • the molar ratio of 1,3- and / or 1,2-propanediol to that or the compounds (b) is usually 0.1: 1 to 8: 1, preferably 1: 1 to 4: 1.
  • Preferred aromatic chain extenders are 1,4-bis (hydroxymethyl) benzene (BHMB), 1,3-bis (hydroxymethyl) benzene, 1,2-bis (hydroxymethyl) benzene, 1,2-bis (2-hydroxyethoxy) benzene, 1,3-bis (2-hydroxyethoxy) benzene, 1,4-bis (2-hydroxyethoxy) benzene (HQEE), diester of terephthalic acid with alkane diols with 2 to 4 carbon atoms, e.g. Terephthalic acid bis-ethanediol or 1,4-butanediol, aromatic diamines such as e.g.
  • 2,4- and 2,6-toluenediamine 3,5-diethyl-2,4- and -2,6-toluenediamine and primary, ortho-di, tri and / or tetraalkyl substituted 4,4'-diamino-diphenylmethane, piperazine and / or Mixtures containing at least two of the aromatic mentioned Chain extenders can be used.
  • 1,4-bis (hydroxymethyl) benzene is particularly preferred as aromatic chain extender used.
  • the molar ratio of aromatic chain extenders to 1,3- and / or 1,2-propanediol is usually 0.01: 1 to 1: 1, preferably 0.05: 1 to 0.55: 1.
  • chain extenders In addition to the chain extenders mentioned, if necessary further, generally known chain extenders (c) are used will be described later as an example become. Are preferred as chain extenders exclusively 1,2- and / or 1,3-propanediol optionally together with at least an aromatic chain extender.
  • the Build-up components (b) and (c) in relatively wide molar ratios can be varied. Molar ratios have proven successful from component (b) to chain extenders to be used overall (c) from 1: 0.5 to 1:12, in particular from 1: 1 to 1: 6.4, the hardness and melting point the TPUs increase with increasing diol content.
  • the implementation with a key figure of ⁇ 104 preferably carried out 104 to 120, particularly preferably 105 to 110.
  • the key figure is defined by the ratio of the total Isocyanate groups of the component used in the reaction (a) to the isocyanate groups, i.e. the active one Hydrogen, the components (b), (c) and optionally (d).
  • a key figure of 100 there is one isocyanate group Component (a) an active hydrogen atom, i.e. one opposite Isocyanate reactive function, the components (b), (c) and optionally (d).
  • the isocyanate index also called the index, is actually that amount of isocyanate groups used divided by the theoretical necessary for the complete implementation of all OH groups Amount of isocyanate groups multiplied by 100.
  • TPUs can according to the known methods in one-shot process continuously on conveyor systems or with reaction extruders as well as discontinuously in the casting process as well according to your known prepolymer process. With these procedures components (a), (b) and optionally (c) one after the other or simultaneously with one another are mixed, the reaction commencing immediately.
  • the implementation is preferably carried out in a one-shot process.
  • reaction mixture can contain (a), (b), (c) and optionally (e) and / or (f) after the Extruder process or preferably implemented by the belt process become.
  • belt process Procedure the following applies to the belt process Procedure:
  • the reaction mixture is placed on a support, preferably conveyor belt, applied and tempered by a Zone led.
  • the reaction temperature in the tempered zone can be 60 to 200 ° C, preferably 100 to 180 ° C and the residence time is generally 0.05 to 0.5 hours, preferably 0.1 to 0.3 hours.
  • the TPU is allowed to cool and crushed or granulated subsequently.
  • TPUs produced according to the invention which are usually present in the form of granules or in powder form, to give the desired cable sheaths, fibers, molded parts, claddings in automobiles, seals, cable plugs, bellows, hoses, foils, rollers, trailing cables, belts or damping elements is carried out using customary methods , such as B. injection molding or extrusion.
  • crosslinked polyisocyanate polyadducts for example soft, semi-hard or hard, compact or cellular, for example microcellular polyurethanes and / or polyisocyanurates
  • compounds (b) with a functionality of 2 to 6 crosslinking agents (d) with a functionality of 3 to 6 and a molecular weight ⁇ 450, preferably 60 to 300
  • blowing agents for example water, fluorocarbons and / or (cyclo) alkanes with a boiling point at 1013 mbar, usually ⁇ 50 ° C.
  • blowing agents for example water, fluorocarbons and / or (cyclo) alkanes with a boiling point at 1013 mbar, usually ⁇ 50 ° C.
  • blowing agents for example water, fluorocarbons and / or (cyclo) alkanes with a boiling point at 1013 mbar, usually ⁇ 50 ° C.
  • the manufacture of these products is generally known.
  • thermoplastic polyurethanes have the desired increased heat resistance.
  • the TPU was produced using the starting components shown in Table 1.
  • the compounds reactive toward isocyanates were initially introduced in the liquid state at a temperature of 100 ° C., in the case of BHMB 110 ° C., and the isocyanate heated to a temperature of 50 ° C. was added, the components being stirred vigorously with one another. After reaching a temperature of 115 ° C, the exothermic reaction mixture was poured into a tray in which it cured at a heating temperature of 120 ° C and a residence time of 20 min. After tempering for 24 hours at 100 ° C, the material was granulated and injection molded at a temperature of 210 ° C, using BHMB 230 ° C, to test specimens.
  • Examples 4 and 5 represent examples according to the invention.
  • the TPUs produced in the examples were checked for their properties, in particular with regard to the heat resistance.
  • the properties of the test specimens are given in Table 2.
  • example density Shore A hardness Vicat temperature Abrasion Tear resistance tensile strenght Elongation at break [g / cm 3 ] [° C] [mm 3 ] [N / mm] [N / mm 2 ] [%] 1 1.18 84 144 35 62 44 510 2nd 1.17 82 138 25th 58 41 420 3rd 1.17 82 156 25th 56 42 400 4th 1.18 84 160 27 67 44 480 5 1.18 84 160 24th 62 48 510 6 1.18 83 128 45 52 44 590 7 1.18 81 144 47 59 30th 580
  • the significantly improved heat resistance of samples 4 and 5 according to the invention are particularly evident from the Vicat temperatures (see also FIG. 1).
  • the Vicat temperature indicates the temperature at which a needle loaded with a weight of 10 N and having a contact surface of 1 mm 2 penetrated 1 mm deep into the sample, which is heated at 120 ° C./h. This measurement is carried out according to DIN EN ISO 306.
  • the properties of the TPUs according to the invention are in the Table 2 shown. The assessment of the State of the art is supported by this data. Only the TPUs produced according to the invention have heat resistance to meet the highest demands. It is clear compared to that of the comparison samples improved. In addition samples 4 and 5 show significantly improved values for the Abrasion and tear resistance, especially compared to the samples that are only made with aromatic chain extenders were prepared (Examples 6 and 7). The production the TPUs with a known, low key figure leads to a Deterioration of heat resistance, tensile strength, des Tear resistance and elongation at break (Examples 2 and 3). Only with 1,4-butanediol as a chain extender TPU produced in particular shows poorer heat resistance and increased abrasion.
  • polyisocyanate polyadducts in particular TPUs with improved properties, especially an improved one Provide heat resistance through which technical teaching according to the invention could be solved.
  • the TPUs according to the invention have a comparison with known TPUs significantly improved properties.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Sealing Material Composition (AREA)
EP99107087A 1998-04-15 1999-04-12 Procédé de préparation de polyuréthanes thermoplastiques Withdrawn EP0950674A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19816525A DE19816525A1 (de) 1998-04-15 1998-04-15 Verfahren zur Herstellung von thermoplastischen Polyurethanen
DE19816525 1998-04-15

Publications (1)

Publication Number Publication Date
EP0950674A1 true EP0950674A1 (fr) 1999-10-20

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EP99107087A Withdrawn EP0950674A1 (fr) 1998-04-15 1999-04-12 Procédé de préparation de polyuréthanes thermoplastiques

Country Status (7)

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EP (1) EP0950674A1 (fr)
JP (1) JPH11322887A (fr)
KR (1) KR19990083197A (fr)
BR (1) BR9901265A (fr)
CA (1) CA2267629A1 (fr)
DE (1) DE19816525A1 (fr)
NO (1) NO991764L (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1409564A1 (fr) * 2001-07-24 2004-04-21 Radicispandex Corporation Compositions spandex ameliorees
US8076445B2 (en) * 2000-01-11 2011-12-13 Robert Shane Porzio Oligocarbodiimides for the formation of crosslinked latex films
WO2014195211A1 (fr) * 2013-06-04 2014-12-11 Basf Se Élastomères de polyuréthane thermoplastique mous et leur procédé de préparation
EP3222644A4 (fr) * 2015-04-01 2018-07-11 Samyang Corporation Polyuréthane, son procédé de préparation et son utilisation
WO2018146336A1 (fr) * 2017-02-13 2018-08-16 Basf Se Polyuréthane thermoplastique
WO2018146335A1 (fr) * 2017-02-13 2018-08-16 Basf Se Polyuréthane thermoplastique
EP3872109A1 (fr) * 2014-03-25 2021-09-01 Basf Se Tuyau pneumatique en tpu

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10053060A1 (de) * 2000-10-26 2002-05-08 Volkswagen Ag Vorrichtung zur Montage einer Scheibe
DE10116592A1 (de) * 2001-04-03 2002-10-17 Getzner Werkstoffe Ges M B H Elastomer II
JP5751169B2 (ja) * 2009-06-02 2015-07-22 宇部興産株式会社 ポリウレタンポリマー溶液及びその製造方法
CN109942788A (zh) * 2019-02-21 2019-06-28 唯万科技有限公司 自润滑耐水解聚氨酯弹性材料及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4517326A (en) * 1981-06-15 1985-05-14 Freeman Chemical Corporation Aqueous liquid filled polyurethane gels and method of making the same
CN1033635A (zh) * 1988-10-13 1989-07-05 中国人民解放军海军工程学院 宽温域高阻尼聚氨酯材料
EP0434467A2 (fr) * 1989-12-22 1991-06-26 The Dow Chemical Company Polyuréthane thermoplastique et son procédé de préparation
US5290036A (en) * 1993-04-12 1994-03-01 Frank Fenton Cavity back iron with vibration dampening material in rear cavity

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4980445A (en) * 1989-01-17 1990-12-25 The Dow Chemical Company Thermoplastic polyurethanes
DE3930838A1 (de) * 1989-09-15 1991-03-28 Bayer Ag Verfahren zur herstellung von tpu-enthaltenden chemiewerkstoffen
US5670601A (en) * 1995-06-15 1997-09-23 Arco Chemical Technology, L.P. Polyurethane elastomers having improved green strength and demold time and polyoxyalkylene polyols suitable for their preparation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4517326A (en) * 1981-06-15 1985-05-14 Freeman Chemical Corporation Aqueous liquid filled polyurethane gels and method of making the same
CN1033635A (zh) * 1988-10-13 1989-07-05 中国人民解放军海军工程学院 宽温域高阻尼聚氨酯材料
EP0434467A2 (fr) * 1989-12-22 1991-06-26 The Dow Chemical Company Polyuréthane thermoplastique et son procédé de préparation
US5290036A (en) * 1993-04-12 1994-03-01 Frank Fenton Cavity back iron with vibration dampening material in rear cavity

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 113, no. 18, 29 October 1990, Columbus, Ohio, US; abstract no. 153663v, XP000191826 *
M.V. PANDA ET AL, JOURNAL OF APPLIED POLYMER SCIENCE, vol. 35, no. 7, 20 May 1988 (1988-05-20), pages 1803 - 1815, XP000160097 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8076445B2 (en) * 2000-01-11 2011-12-13 Robert Shane Porzio Oligocarbodiimides for the formation of crosslinked latex films
EP1409564A1 (fr) * 2001-07-24 2004-04-21 Radicispandex Corporation Compositions spandex ameliorees
EP1409564A4 (fr) * 2001-07-24 2006-05-03 Radicispandex Corp Compositions spandex ameliorees
WO2014195211A1 (fr) * 2013-06-04 2014-12-11 Basf Se Élastomères de polyuréthane thermoplastique mous et leur procédé de préparation
EP3872109A1 (fr) * 2014-03-25 2021-09-01 Basf Se Tuyau pneumatique en tpu
EP3222644A4 (fr) * 2015-04-01 2018-07-11 Samyang Corporation Polyuréthane, son procédé de préparation et son utilisation
WO2018146336A1 (fr) * 2017-02-13 2018-08-16 Basf Se Polyuréthane thermoplastique
WO2018146335A1 (fr) * 2017-02-13 2018-08-16 Basf Se Polyuréthane thermoplastique
US11306177B2 (en) 2017-02-13 2022-04-19 Basf Se Thermoplastic polyurethane

Also Published As

Publication number Publication date
NO991764L (no) 1999-10-18
BR9901265A (pt) 2000-03-21
JPH11322887A (ja) 1999-11-26
CA2267629A1 (fr) 1999-10-15
DE19816525A1 (de) 1999-10-21
NO991764D0 (no) 1999-04-14
KR19990083197A (ko) 1999-11-25

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